JP2023514725A - 化合物および使用方法 - Google Patents

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Publication number

JP2023514725A

JP2023514725A JP2022550164A JP2022550164A JP2023514725A JP 2023514725 A JP2023514725 A JP 2023514725A JP 2022550164 A JP2022550164 A JP 2022550164A JP 2022550164 A JP2022550164 A JP 2022550164A JP 2023514725 A JP2023514725 A JP 2023514725A

Authority

JP

Japan

Prior art keywords

alkylene

carboxamide

naphthyridin

oxy

membered

Prior art date

2020-02-24

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 261
• 238000000034 method Methods 0.000 title claims abstract description 61
• 150000003839 salts Chemical class 0.000 claims abstract description 133
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 12
• 108060006633 protein kinase Proteins 0.000 claims abstract description 12
• 230000001404 mediated effect Effects 0.000 claims abstract description 7
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 431
• 125000000217 alkyl group Chemical group 0.000 claims description 226
• 125000001072 heteroaryl group Chemical group 0.000 claims description 199
• 125000001424 substituent group Chemical group 0.000 claims description 190
• -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 170
• 125000003118 aryl group Chemical group 0.000 claims description 143
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 133
• 125000002947 alkylene group Chemical group 0.000 claims description 123
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 107
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 96
• 125000005843 halogen group Chemical group 0.000 claims description 93
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 92
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 90
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 89
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 83
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 77
• 125000004429 atom Chemical group 0.000 claims description 72
• 229910052739 hydrogen Inorganic materials 0.000 claims description 68
• 229910052799 carbon Inorganic materials 0.000 claims description 64
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 61
• 229910052757 nitrogen Inorganic materials 0.000 claims description 60
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 60
• 125000004432 carbon atom Chemical group C* 0.000 claims description 57
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 54
• 201000010099 disease Diseases 0.000 claims description 54
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 53
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 49
• 101150073096 NRAS gene Proteins 0.000 claims description 48
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 45
• 125000003545 alkoxy group Chemical group 0.000 claims description 43
• 125000005842 heteroatom Chemical group 0.000 claims description 40
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 38
• 208000035475 disorder Diseases 0.000 claims description 35
• DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 33
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 29
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
• 239000011570 nicotinamide Substances 0.000 claims description 22
• 235000005152 nicotinamide Nutrition 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 125000006239 protecting group Chemical group 0.000 claims description 20
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 238000001727 in vivo Methods 0.000 claims description 15
• 230000000694 effects Effects 0.000 claims description 14
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 12
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 12
• 229910017711 NHRa Inorganic materials 0.000 claims description 12
• 229910052702 rhenium Inorganic materials 0.000 claims description 12
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 6
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 6
• 208000011580 syndromic disease Diseases 0.000 claims description 6
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 5
• RRTCBGOYXHZCAR-UHFFFAOYSA-N C(C)(=O)C=1C=C(C(N(C=1C)C1=NC=C(C=C1)F)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F Chemical compound C(C)(=O)C=1C=C(C(N(C=1C)C1=NC=C(C=C1)F)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F RRTCBGOYXHZCAR-UHFFFAOYSA-N 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 229920002554 vinyl polymer Polymers 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• WRRAGWMDUHXSGV-UHFFFAOYSA-N BrC=1C=C(C(N(C=1C)C1=NC=C(C=C1)F)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F Chemical compound BrC=1C=C(C(N(C=1C)C1=NC=C(C=C1)F)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F WRRAGWMDUHXSGV-UHFFFAOYSA-N 0.000 claims description 3
• GJXJZMWGINQVJY-UHFFFAOYSA-N C(#N)C=1C=C(C(N(C=1C)C1=NC=C(C=C1)F)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F Chemical compound C(#N)C=1C=C(C(N(C=1C)C1=NC=C(C=C1)F)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F GJXJZMWGINQVJY-UHFFFAOYSA-N 0.000 claims description 3
• DYMDUGMJTGDBRJ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O)F DYMDUGMJTGDBRJ-UHFFFAOYSA-N 0.000 claims description 3
• FMTVXXZRSORBKW-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1C)F)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1C)F)=O)F FMTVXXZRSORBKW-UHFFFAOYSA-N 0.000 claims description 3
• JFSNCNQJVPSPNY-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=NC=C(C=C1)F)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=NC=C(C=C1)F)=O)F JFSNCNQJVPSPNY-UHFFFAOYSA-N 0.000 claims description 3
• ZGBROHJPEHYZNG-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1C)C1=NC=C(C=C1)F)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1C)C1=NC=C(C=C1)F)=O)F ZGBROHJPEHYZNG-UHFFFAOYSA-N 0.000 claims description 3
• JZMMZVZTTYZPKX-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=CC=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=CC=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O JZMMZVZTTYZPKX-UHFFFAOYSA-N 0.000 claims description 3
• WVPYBHGBEFNTMT-UHFFFAOYSA-N FC=1C=C(C=CC=1OC1=CC=NC2=CC(=C(N=C12)OC)OCCOC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O Chemical compound FC=1C=C(C=CC=1OC1=CC=NC2=CC(=C(N=C12)OC)OCCOC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O WVPYBHGBEFNTMT-UHFFFAOYSA-N 0.000 claims description 3
• HHBJXKRKZSUJRG-UHFFFAOYSA-N FC=1C=C(C=CC=1OC1=CC=NC2=CC(=CN=C12)OC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1C)F)=O Chemical compound FC=1C=C(C=CC=1OC1=CC=NC2=CC(=CN=C12)OC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1C)F)=O HHBJXKRKZSUJRG-UHFFFAOYSA-N 0.000 claims description 3
• YQYYJRYQYXHJOC-UHFFFAOYSA-N FC=1C=C(C=CC=1OC1=CC=NC2=CC=C(N=C12)OC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1C)F)=O Chemical compound FC=1C=C(C=CC=1OC1=CC=NC2=CC=C(N=C12)OC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1C)F)=O YQYYJRYQYXHJOC-UHFFFAOYSA-N 0.000 claims description 3
• VKLHKXQQQQLKFW-UHFFFAOYSA-N FC=1C=CC(=NC=1)N1C(C(=CC=C1C)C(=O)NC1=CC=C(C=C1)OC1=CC=NC2=CC(=CN=C12)OC)=O Chemical compound FC=1C=CC(=NC=1)N1C(C(=CC=C1C)C(=O)NC1=CC=C(C=C1)OC1=CC=NC2=CC(=CN=C12)OC)=O VKLHKXQQQQLKFW-UHFFFAOYSA-N 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• SMTVNBUXPYDFGP-UHFFFAOYSA-N FC=1C=C(C=CC=1OC1=CC=NC2=CC=C(C=C12)OC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O Chemical compound FC=1C=C(C=CC=1OC1=CC=NC2=CC=C(C=C12)OC)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O SMTVNBUXPYDFGP-UHFFFAOYSA-N 0.000 claims description 2
• HJEYCGMJTBRCCG-UHFFFAOYSA-N FC=1C=C(C=CC=1OC1=CC=NC2=CC=CN=C12)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O Chemical compound FC=1C=C(C=CC=1OC1=CC=NC2=CC=CN=C12)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)F)=O HJEYCGMJTBRCCG-UHFFFAOYSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 125000006352 iso-propylthiomethyl group Chemical group [H]C([H])([H])C([H])(SC([H])([H])*)C([H])([H])[H] 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
• 150000003857 carboxamides Chemical class 0.000 claims 4
• FDUPJYPZZSJULC-UHFFFAOYSA-N C(C)(=O)C=1C=C(C(N(C=1C)C1=COC=C1)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F Chemical compound C(C)(=O)C=1C=C(C(N(C=1C)C1=COC=C1)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F FDUPJYPZZSJULC-UHFFFAOYSA-N 0.000 claims 1
• SSNIUBPJRKTNDX-UHFFFAOYSA-N C(C)(=O)C=1C=C(C(N(C=1C)C1=COC=C1)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=CN=C12)OC)F Chemical compound C(C)(=O)C=1C=C(C(N(C=1C)C1=COC=C1)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=CN=C12)OC)F SSNIUBPJRKTNDX-UHFFFAOYSA-N 0.000 claims 1
• QIVCMQDDWZIOJC-UHFFFAOYSA-N C(C)(=O)C=1C=C(C(N(C=1C)C1=COC=C1)=O)C(=O)NC1=CC=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC Chemical compound C(C)(=O)C=1C=C(C(N(C=1C)C1=COC=C1)=O)C(=O)NC1=CC=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC QIVCMQDDWZIOJC-UHFFFAOYSA-N 0.000 claims 1
• RDZATSDEBOICMR-UHFFFAOYSA-N C(C)(=O)C=1C=C(C(N(C=1C)C1=CSC=C1)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F Chemical compound C(C)(=O)C=1C=C(C(N(C=1C)C1=CSC=C1)=O)C(=O)NC1=CC(=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC)F RDZATSDEBOICMR-UHFFFAOYSA-N 0.000 claims 1
• IQXVDRMNHDFBDW-UHFFFAOYSA-N C(C)(=O)C=1C=C(C(N(C=1C)C1=CSC=C1)=O)C(=O)NC1=CC=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC Chemical compound C(C)(=O)C=1C=C(C(N(C=1C)C1=CSC=C1)=O)C(=O)NC1=CC=C(C=C1)OC1=CC=NC2=CC(=C(N=C12)OC)OC IQXVDRMNHDFBDW-UHFFFAOYSA-N 0.000 claims 1
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• SUOADZSNKOVLCM-UHFFFAOYSA-N C1(CCC1)CCOC1=C(N=C2C(=CC=NC2=C1)OC1=C(C=C(C=C1)NC(=O)C1=C(N(C(=C(C1=O)C=1OC=CC=1)C)C)C)F)OC Chemical compound C1(CCC1)CCOC1=C(N=C2C(=CC=NC2=C1)OC1=C(C=C(C=C1)NC(=O)C1=C(N(C(=C(C1=O)C=1OC=CC=1)C)C)C)F)OC SUOADZSNKOVLCM-UHFFFAOYSA-N 0.000 claims 1
• WSOSKVGBPHILOG-UHFFFAOYSA-N COC1=CN=C2C(=CC=NC2=C1)OC1=CC=C(C=C1)NC(=O)C1=C(N(C(=C(C1=O)C=1SC=CC=1)C)C)C Chemical compound COC1=CN=C2C(=CC=NC2=C1)OC1=CC=C(C=C1)NC(=O)C1=C(N(C(=C(C1=O)C=1SC=CC=1)C)C)C WSOSKVGBPHILOG-UHFFFAOYSA-N 0.000 claims 1
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• QGBACIRBSXTYRL-UHFFFAOYSA-N COC=1C=C2C(=CC=NC2=CC=1OC)OC1=CC=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1OC=CC=1)C Chemical compound COC=1C=C2C(=CC=NC2=CC=1OC)OC1=CC=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1OC=CC=1)C QGBACIRBSXTYRL-UHFFFAOYSA-N 0.000 claims 1
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• YCHBZBDEGJSENQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C1=NC=CN(C1=O)C1=NC=C(C=C1)F)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C1=NC=CN(C1=O)C1=NC=C(C=C1)F)F YCHBZBDEGJSENQ-UHFFFAOYSA-N 0.000 claims 1
• LJSPFLNHXXRMBY-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=CC(=NC=C1)C)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=CC(=NC=C1)C)C)COC)F LJSPFLNHXXRMBY-UHFFFAOYSA-N 0.000 claims 1
• RFRQTOXIHVPNHB-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=COC=C1)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=COC=C1)C)C)F RFRQTOXIHVPNHB-UHFFFAOYSA-N 0.000 claims 1
• QUXDARPBNIOAJY-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=CSC=C1)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=CSC=C1)C)C)F QUXDARPBNIOAJY-UHFFFAOYSA-N 0.000 claims 1
• ZYMPUZQVOUJIPC-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC(=CC=C1)C)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC(=CC=C1)C)C)COC)F ZYMPUZQVOUJIPC-UHFFFAOYSA-N 0.000 claims 1
• ZMTXBLJYWFUGGL-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=C(C=C1)F)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=C(C=C1)F)C)C)F ZMTXBLJYWFUGGL-UHFFFAOYSA-N 0.000 claims 1
• PMXLNVRCGZRRCI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=C(C=C1)F)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=C(C=C1)F)C)COC)F PMXLNVRCGZRRCI-UHFFFAOYSA-N 0.000 claims 1
• NRKPZVPSOAWZRK-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=CC=C1)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=CC=C1)C)COC)F NRKPZVPSOAWZRK-UHFFFAOYSA-N 0.000 claims 1
• XTXWWQATYWKIRG-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=CC=C1C)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C1=NC=CC=C1C)C)COC)F XTXWWQATYWKIRG-UHFFFAOYSA-N 0.000 claims 1
• NZBULONFLIMTFF-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=C(C=1)C(F)(F)F)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=C(C=1)C(F)(F)F)C)C)C)F NZBULONFLIMTFF-UHFFFAOYSA-N 0.000 claims 1
• YAYPSEHENYFRMO-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=C(C=1)C)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=C(C=1)C)C)C)C)F YAYPSEHENYFRMO-UHFFFAOYSA-N 0.000 claims 1
• XHOLEZFIHKUXQM-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=CC=1)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1N(N=CC=1)C)C)C)F XHOLEZFIHKUXQM-UHFFFAOYSA-N 0.000 claims 1
• ZLILHVHPHQIFNH-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C(C)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C(C)C)C)C)F ZLILHVHPHQIFNH-UHFFFAOYSA-N 0.000 claims 1
• IDBDLBJTXXUNNF-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C)C)C)F IDBDLBJTXXUNNF-UHFFFAOYSA-N 0.000 claims 1
• NTUBTAFVRFOTKB-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)C)C)COC)F NTUBTAFVRFOTKB-UHFFFAOYSA-N 0.000 claims 1
• WBWJWWLNCBKNEE-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)CC)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC(=CC=1)CC)C)C)F WBWJWWLNCBKNEE-UHFFFAOYSA-N 0.000 claims 1
• YFIFHLLPPDAGOR-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC=CC=1)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC=CC=1)C)C)F YFIFHLLPPDAGOR-UHFFFAOYSA-N 0.000 claims 1
• ACXICGZPGAFENQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC=CC=1)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1OC=CC=1)C)COC)F ACXICGZPGAFENQ-UHFFFAOYSA-N 0.000 claims 1
• FQDZTNLTAQVKMH-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC(=CC=1)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC(=CC=1)C)C)C)F FQDZTNLTAQVKMH-UHFFFAOYSA-N 0.000 claims 1
• AYVRNMNTNVVTAQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=C(C=1)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=C(C=1)C)C)C)F AYVRNMNTNVVTAQ-UHFFFAOYSA-N 0.000 claims 1
• SOXSIADXNGIVSR-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1)C)C)F SOXSIADXNGIVSR-UHFFFAOYSA-N 0.000 claims 1
• SAFRJKACTVWZNI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1)C)COC)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1)C)COC)F SAFRJKACTVWZNI-UHFFFAOYSA-N 0.000 claims 1
• XPPPAYILDZVWNR-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC(=C(C=1O)C=1SC=CC=1C)C)C)F XPPPAYILDZVWNR-UHFFFAOYSA-N 0.000 claims 1
• PRHLPMRAYYNIQI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=COC=C1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=COC=C1)C)F PRHLPMRAYYNIQI-UHFFFAOYSA-N 0.000 claims 1
• KQVXJJAGJJAWKW-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=CSC=C1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=CSC=C1)C)F KQVXJJAGJJAWKW-UHFFFAOYSA-N 0.000 claims 1
• AJTPBFVCPCWIKT-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=C(C=C1)F)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=C(C=C1)F)C)F AJTPBFVCPCWIKT-UHFFFAOYSA-N 0.000 claims 1
• XQNLYFGQTVYCNK-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=C(C=C1C)F)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=C(C=C1C)F)C)F XQNLYFGQTVYCNK-UHFFFAOYSA-N 0.000 claims 1
• MACISLSDGXPVLR-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=CC=C1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C1=NC=CC=C1)C)F MACISLSDGXPVLR-UHFFFAOYSA-N 0.000 claims 1
• SOSHSOQTLMUPAE-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1C=NC=CC=1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1C=NC=CC=1)C)F SOSHSOQTLMUPAE-UHFFFAOYSA-N 0.000 claims 1
• LVGUAFKGPHSORA-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1OC(=CC=1)C=O)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1OC(=CC=1)C=O)C)F LVGUAFKGPHSORA-UHFFFAOYSA-N 0.000 claims 1
• SSWRSRRADIWLCR-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1OC=CC=1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1OC=CC=1)C)F SSWRSRRADIWLCR-UHFFFAOYSA-N 0.000 claims 1
• NMUKNJIKUPGQME-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1SC=CC=1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(=NC=C(C=1O)C=1SC=CC=1)C)F NMUKNJIKUPGQME-UHFFFAOYSA-N 0.000 claims 1
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• LLXXBVQTLMYOIE-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1OC=CC=1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1OC=CC=1)=O)F LLXXBVQTLMYOIE-UHFFFAOYSA-N 0.000 claims 1
• UCVGDUJGIMWBTI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC(=CC=1)C)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC(=CC=1)C)=O)F UCVGDUJGIMWBTI-UHFFFAOYSA-N 0.000 claims 1
• ZTPPMOXJBDVHDZ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC=C(C=1)C)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC=C(C=1)C)=O)F ZTPPMOXJBDVHDZ-UHFFFAOYSA-N 0.000 claims 1
• JYCSPQOEJLFNRL-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC=CC=1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(C(=CN2C=1COCC2)C=1SC=CC=1)=O)F JYCSPQOEJLFNRL-UHFFFAOYSA-N 0.000 claims 1
• FHGACBYGUZSSGN-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=C(C=NC=C1)F)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=C(C=NC=C1)F)=O)F FHGACBYGUZSSGN-UHFFFAOYSA-N 0.000 claims 1
• VLGRKRXTELZQMQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)C)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)C)=O)F VLGRKRXTELZQMQ-UHFFFAOYSA-N 0.000 claims 1
• TXBYEKNRJRLLEN-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)F)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)F)=O)F TXBYEKNRJRLLEN-UHFFFAOYSA-N 0.000 claims 1
• JXAVEKZMGZHAQX-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)O)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)O)=O)F JXAVEKZMGZHAQX-UHFFFAOYSA-N 0.000 claims 1
• AQNPSEJLYYRKFQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OC(C)C)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OC(C)C)=O)F AQNPSEJLYYRKFQ-UHFFFAOYSA-N 0.000 claims 1
• PQFBNURKUROABN-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OC)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OC)=O)F PQFBNURKUROABN-UHFFFAOYSA-N 0.000 claims 1
• YNHAHAOLJMMCDL-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OCCOCCOCC)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC(=NC=C1)OCCOCCOCC)=O)F YNHAHAOLJMMCDL-UHFFFAOYSA-N 0.000 claims 1
• DULMLQKOCHQMDQ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC=NC=C1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC=NC=C1)=O)F DULMLQKOCHQMDQ-UHFFFAOYSA-N 0.000 claims 1
• XTEAASMSMMAXJE-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC=[N+](C=C1)[O-])=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=CC=[N+](C=C1)[O-])=O)F XTEAASMSMMAXJE-UHFFFAOYSA-N 0.000 claims 1
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• BNMBIJKZZRAHCI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)OCC)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C1=NC=C(C=C1)OCC)=O)F BNMBIJKZZRAHCI-UHFFFAOYSA-N 0.000 claims 1
• JVYUOHPIMNJQNE-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C=1C=NC=CC=1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C=1C=NC=CC=1)=O)F JVYUOHPIMNJQNE-UHFFFAOYSA-N 0.000 claims 1
• CUZNXKBGCZNZNP-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C=1N=NC=CC=1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(=CC=1)C)C=1N=NC=CC=1)=O)F CUZNXKBGCZNZNP-UHFFFAOYSA-N 0.000 claims 1
• PLYDGFZRLONKPP-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC(=NC=C1)O)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC(=NC=C1)O)=O)F PLYDGFZRLONKPP-UHFFFAOYSA-N 0.000 claims 1
• REEHLFPGCWNRRS-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC=NC=C1)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC=NC=C1)=O)F REEHLFPGCWNRRS-UHFFFAOYSA-N 0.000 claims 1
• CJMUTKWRGXBZMI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC=[N+](C=C1)[O-])=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1)C1=CC=[N+](C=C1)[O-])=O)F CJMUTKWRGXBZMI-UHFFFAOYSA-N 0.000 claims 1
• WXGRPEIXNHMYHY-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1OCC)C1=NC=C(C=C1)F)=O)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C=CC=1OCC)C1=NC=C(C=C1)F)=O)F WXGRPEIXNHMYHY-UHFFFAOYSA-N 0.000 claims 1
• NWOUOFPZTLZRBO-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=CN=CS1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=CN=CS1)C)F NWOUOFPZTLZRBO-UHFFFAOYSA-N 0.000 claims 1
• NEFMRZONQLCBLZ-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=COC=C1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=COC=C1)C)F NEFMRZONQLCBLZ-UHFFFAOYSA-N 0.000 claims 1
• KVWOLBLGONMBMO-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=CSC=C1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=CSC=C1)C)F KVWOLBLGONMBMO-UHFFFAOYSA-N 0.000 claims 1
• XPNPZUCFVYALRK-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=NC=C(C=C1)F)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C1=NC=C(C=C1)F)C)F XPNPZUCFVYALRK-UHFFFAOYSA-N 0.000 claims 1
• AQBBFGCOJJASCG-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1C=NOC=1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1C=NOC=1)C)F AQBBFGCOJJASCG-UHFFFAOYSA-N 0.000 claims 1
• GXPYXVFGHQYIML-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N(N=C(C=1)C(F)(F)F)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N(N=C(C=1)C(F)(F)F)C)C)F GXPYXVFGHQYIML-UHFFFAOYSA-N 0.000 claims 1
• PMLHAPGDYAOKCH-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N(N=C(C=1)C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N(N=C(C=1)C)C)C)F PMLHAPGDYAOKCH-UHFFFAOYSA-N 0.000 claims 1
• ILMLBRHNNSVSCT-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N=CSC=1)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1N=CSC=1)C)F ILMLBRHNNSVSCT-UHFFFAOYSA-N 0.000 claims 1
• AMOMCGMVSNWTMI-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1OC(=CC=1)C(=C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1OC(=CC=1)C(=C)C)C)F AMOMCGMVSNWTMI-UHFFFAOYSA-N 0.000 claims 1
• DWRPNQLZTKLVSH-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1OC(=CC=1)C(C)C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1OC(=CC=1)C(C)C)C)F DWRPNQLZTKLVSH-UHFFFAOYSA-N 0.000 claims 1
• UWUMYGSHQFQEMM-UHFFFAOYSA-N COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1OC(=CC=1)C=C)C)F Chemical compound COC=1N=C2C(=CC=NC2=CC=1OC)OC1=C(C=C(C=C1)NC(=O)C=1C=NC(=C(C=1O)C=1OC(=CC=1)C=C)C)F UWUMYGSHQFQEMM-UHFFFAOYSA-N 0.000 claims 1
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